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In the ionic structure of the title compound, [Fe(C12H8N2)3](C9H5N4O2)2·H2O, the octa­hedral tris-chelate [Fe(phen)3]2+ dications [Fe—N = 1.9647 (14)–1.9769 (14) Å; phen is 1,10-phenathroline] afford one-dimensional chains by a series of slipped π–π stacking inter­actions [centroid-to-centroid dis­tances = 3.792 (3) and 3.939 (3) Å]. The 1,1,3,3-tetra­cyano-2-(2-hy­droxy­ethyl)propenide anions, denoted tcnoetOH, reveal an appreciable delocalization of π-electron density, involving the central propenide [C—C = 1.383 (3)–1.401 (2) Å] fragment and four nitrile groups, and this is also supported by density functional theory (DFT) calculations at the B97D/6-311+G(2d,2p) level. Primary noncovalent inter-moiety inter­actions comprise conventional O—H...O(N) and weak C—H...O(N) hydrogen bonding [O...O(N) = 2.833 (2)–3.289 (5) Å and C...O(N) = 3.132 (2)–3.439 (2) Å]. The double anion...π inter­action involving a nitrile group of tcnoetOH and two cis-positioned pyridine rings (`π-pocket') of [Fe(phen)3]2+ [N...centroid = 3.212 (2) and 3.418 (2) Å] suggest the relevance of anion...π stackings for charge-diffuse polycyano­anions and common M-chelate species.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113027108/fg3309sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113027108/fg3309Isup2.hkl
Contains datablock I

CCDC reference: 964427

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).

Tris(1,10-phenanthroline-κ2N,N')iron(II) bis[1,1,3,3-tetracyano-2-(2-hydroxyethyl)propenide] monohydrate top
Crystal data top
[Fe(C12H8N2)3](C9H5N4O2)2·H2OZ = 2
Mr = 1016.82F(000) = 1048
Triclinic, P1Dx = 1.417 Mg m3
a = 9.8498 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.9871 (3) ÅCell parameters from 12148 reflections
c = 18.8001 (4) Åθ = 3.7–29.3°
α = 83.7705 (18)°µ = 0.38 mm1
β = 89.3525 (18)°T = 120 K
γ = 85.6990 (17)°Prism, red
V = 2383.97 (9) Å30.35 × 0.35 × 0.15 mm
Data collection top
Agilent Xcalibur
diffractometer
10732 independent reflections
Radiation source: fine-focus sealed tube9151 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: gaussian
(CrysAlis PRO; Agilent, 2013)
h = 1212
Tmin = 0.789, Tmax = 0.945k = 1616
34906 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0371P)2 + 2.1221P]
where P = (Fo2 + 2Fc2)/3
10732 reflections(Δ/σ)max = 0.001
704 parametersΔρmax = 0.76 e Å3
32 restraintsΔρmin = 0.66 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.59379 (2)0.538465 (18)0.251541 (12)0.01471 (7)
O10.96427 (12)0.02118 (9)0.14394 (7)0.0240 (3)
O20.92939 (17)0.21771 (12)0.19213 (9)0.0447 (4)
H1O0.85760.19810.17470.067*
O1W0.66432 (15)0.16739 (12)0.15859 (8)0.0394 (4)
H1W0.66240.14070.11930.059*
H2W0.58340.17440.17440.059*
N10.73687 (13)0.60217 (11)0.30025 (7)0.0159 (3)
N20.55618 (14)0.68082 (11)0.20557 (7)0.0169 (3)
N30.45420 (14)0.48096 (11)0.19595 (7)0.0169 (3)
N40.71209 (13)0.50262 (10)0.17098 (7)0.0160 (3)
N50.46658 (13)0.56023 (11)0.33122 (7)0.0177 (3)
N60.63230 (13)0.40115 (11)0.30678 (7)0.0171 (3)
N70.8041 (2)0.26357 (15)0.04203 (11)0.0450 (5)
N80.7404 (2)0.07197 (16)0.01265 (11)0.0468 (5)
N91.18717 (18)0.14473 (13)0.27743 (9)0.0313 (4)
N101.12569 (16)0.32841 (13)0.10975 (9)0.0291 (4)
N110.0528 (2)0.39363 (19)0.30337 (14)0.0673 (8)
N120.41826 (19)0.21370 (16)0.24398 (10)0.0420 (5)
N130.1539 (3)0.0235 (2)0.55767 (12)0.0620 (7)
N140.0578 (2)0.3139 (2)0.46717 (11)0.0589 (7)
C10.73540 (16)0.70693 (13)0.28219 (8)0.0161 (3)
C20.82943 (17)0.55889 (14)0.34771 (9)0.0193 (3)
H20.83250.48600.36090.023*
C30.92241 (18)0.61704 (15)0.37890 (9)0.0231 (4)
H30.98720.58340.41240.028*
C40.92016 (17)0.72225 (15)0.36118 (9)0.0233 (4)
H40.98270.76200.38240.028*
C50.82392 (17)0.77084 (14)0.31111 (9)0.0196 (3)
C60.81197 (18)0.87989 (14)0.28742 (10)0.0236 (4)
H60.87030.92440.30710.028*
C70.71943 (18)0.92068 (14)0.23760 (10)0.0231 (4)
H70.71440.99310.22270.028*
C80.62858 (17)0.85624 (13)0.20681 (9)0.0201 (3)
C90.53096 (18)0.89252 (14)0.15422 (10)0.0242 (4)
H90.52140.96400.13630.029*
C100.44959 (18)0.82320 (15)0.12906 (10)0.0248 (4)
H100.38330.84640.09340.030*
C110.46460 (17)0.71842 (14)0.15606 (9)0.0212 (3)
H110.40680.67180.13820.025*
C120.63765 (16)0.74992 (13)0.22994 (8)0.0168 (3)
C130.50599 (16)0.44094 (12)0.13640 (9)0.0167 (3)
C140.32206 (17)0.47443 (13)0.20872 (9)0.0203 (3)
H140.28370.50140.25010.024*
C150.23711 (17)0.42934 (14)0.16361 (10)0.0227 (4)
H150.14300.42650.17470.027*
C160.28861 (18)0.38940 (14)0.10375 (10)0.0226 (4)
H160.23100.35930.07290.027*
C170.42813 (17)0.39367 (13)0.08873 (9)0.0193 (3)
C180.49476 (18)0.35370 (14)0.02829 (10)0.0240 (4)
H180.44370.32060.00400.029*
C190.62960 (19)0.36249 (14)0.01650 (9)0.0236 (4)
H190.67200.33370.02320.028*
C200.70943 (17)0.41443 (13)0.06287 (9)0.0192 (3)
C210.84730 (17)0.43195 (14)0.05105 (9)0.0215 (3)
H210.89530.40630.01170.026*
C220.91122 (17)0.48700 (14)0.09757 (9)0.0209 (3)
H221.00310.50270.08920.025*
C230.84133 (17)0.51993 (13)0.15718 (9)0.0189 (3)
H230.88840.55630.18920.023*
C240.64661 (16)0.45213 (12)0.12285 (8)0.0165 (3)
C250.46238 (16)0.47442 (14)0.37975 (9)0.0188 (3)
C260.38477 (17)0.64349 (14)0.34285 (9)0.0223 (4)
H260.38650.70430.31000.027*
C270.29649 (18)0.64445 (16)0.40179 (10)0.0275 (4)
H270.24030.70540.40840.033*
C280.29101 (18)0.55802 (17)0.44974 (10)0.0286 (4)
H280.23050.55820.48940.034*
C290.37585 (18)0.46885 (15)0.43968 (9)0.0239 (4)
C300.3808 (2)0.37399 (17)0.48643 (10)0.0305 (4)
H300.32160.36850.52670.037*
C310.4676 (2)0.29228 (16)0.47449 (10)0.0304 (4)
H310.46890.23060.50670.037*
C320.55820 (19)0.29663 (14)0.41407 (10)0.0240 (4)
C330.6534 (2)0.21571 (15)0.39900 (10)0.0287 (4)
H330.66130.15240.42960.034*
C340.73433 (19)0.22933 (14)0.33967 (11)0.0273 (4)
H340.79960.17540.32910.033*
C350.72123 (17)0.32269 (13)0.29429 (10)0.0210 (3)
H350.77790.33020.25310.025*
C360.55274 (17)0.38776 (13)0.36669 (9)0.0191 (3)
C370.84090 (19)0.18682 (16)0.05638 (10)0.0283 (4)
C380.87932 (18)0.08890 (14)0.07257 (9)0.0220 (4)
C390.8037 (2)0.00052 (16)0.03914 (10)0.0296 (4)
C400.97440 (17)0.07576 (13)0.12490 (9)0.0188 (3)
C411.06695 (17)0.15301 (13)0.15784 (9)0.0197 (3)
C421.09606 (17)0.24945 (14)0.12995 (9)0.0208 (3)
C431.13246 (17)0.14552 (13)0.22383 (10)0.0219 (4)
C441.08005 (19)0.07166 (14)0.16574 (12)0.0292 (4)
H44A1.16200.05190.13790.035*
H44B1.09900.05240.21730.035*
C451.0411 (2)0.18589 (15)0.15097 (13)0.0360 (5)
H45A1.11980.22500.16130.043*
H45B1.01880.20260.09960.043*
C460.1298 (2)0.32366 (18)0.31953 (13)0.0418 (5)
C470.2262 (2)0.23829 (17)0.33580 (11)0.0325 (4)
C480.3335 (2)0.22526 (17)0.28522 (12)0.0347 (5)
C490.2233 (2)0.17089 (18)0.39795 (12)0.0372 (5)
C500.1305 (2)0.17046 (19)0.45441 (11)0.0370 (5)
C510.0254 (2)0.2497 (2)0.46010 (11)0.0414 (6)
C520.1435 (2)0.0892 (2)0.51145 (13)0.0453 (6)
O3A0.33382 (17)0.09998 (13)0.40821 (9)0.0309 (4)0.858 (3)
O4A0.5220 (4)0.0677 (2)0.43724 (16)0.0944 (12)0.858 (3)
H2OA0.60550.05490.43590.142*0.858 (3)
C53A0.3222 (3)0.0086 (2)0.37385 (16)0.0421 (6)0.858 (3)
H53A0.28270.02640.32550.051*0.858 (3)
H53B0.26330.03920.40210.051*0.858 (3)
C54A0.4650 (3)0.04052 (19)0.36923 (14)0.0361 (6)0.858 (3)
H54A0.46380.10350.34390.043*0.858 (3)
H54B0.52230.00870.34110.043*0.858 (3)
O3B0.2652 (10)0.0665 (5)0.3893 (6)0.039 (2)0.142 (3)
O4B0.4294 (9)0.1314 (7)0.3724 (5)0.027 (2)0.142 (3)
H2OB0.34900.12260.35580.041*0.142 (3)
C53B0.4007 (12)0.0332 (9)0.4125 (9)0.036 (2)0.142 (3)
H53C0.41970.07130.45370.043*0.142 (3)
H53D0.46300.05700.37340.043*0.142 (3)
C54B0.4413 (19)0.0804 (9)0.4344 (7)0.044 (2)0.142 (3)
H54C0.53610.08940.45220.053*0.142 (3)
H54D0.38030.10870.47270.053*0.142 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.01306 (11)0.01616 (12)0.01518 (11)0.00012 (8)0.00211 (8)0.00338 (9)
O10.0212 (6)0.0162 (6)0.0351 (7)0.0002 (5)0.0033 (5)0.0064 (5)
O20.0461 (9)0.0316 (8)0.0591 (10)0.0027 (7)0.0069 (8)0.0216 (8)
O1W0.0382 (8)0.0388 (9)0.0381 (8)0.0089 (7)0.0078 (7)0.0009 (7)
N10.0150 (6)0.0181 (7)0.0148 (6)0.0009 (5)0.0004 (5)0.0034 (5)
N20.0154 (6)0.0196 (7)0.0160 (6)0.0003 (5)0.0017 (5)0.0040 (5)
N30.0154 (6)0.0163 (7)0.0189 (7)0.0003 (5)0.0017 (5)0.0022 (5)
N40.0156 (6)0.0165 (7)0.0162 (6)0.0010 (5)0.0029 (5)0.0022 (5)
N50.0140 (6)0.0214 (7)0.0180 (7)0.0006 (5)0.0028 (5)0.0049 (6)
N60.0144 (6)0.0180 (7)0.0194 (7)0.0016 (5)0.0025 (5)0.0040 (5)
N70.0437 (11)0.0394 (11)0.0549 (12)0.0014 (9)0.0248 (10)0.0169 (9)
N80.0474 (12)0.0452 (12)0.0437 (11)0.0073 (9)0.0179 (9)0.0082 (9)
N90.0362 (9)0.0267 (9)0.0314 (9)0.0032 (7)0.0123 (7)0.0065 (7)
N100.0251 (8)0.0263 (9)0.0376 (9)0.0025 (6)0.0035 (7)0.0132 (7)
N110.0575 (14)0.0568 (15)0.0784 (17)0.0228 (12)0.0378 (13)0.0123 (13)
N120.0348 (10)0.0482 (12)0.0390 (10)0.0151 (8)0.0063 (8)0.0004 (9)
N130.0802 (17)0.0701 (16)0.0325 (11)0.0194 (13)0.0019 (11)0.0088 (11)
N140.0460 (12)0.0965 (19)0.0328 (10)0.0298 (12)0.0027 (9)0.0241 (11)
C10.0156 (7)0.0190 (8)0.0142 (7)0.0009 (6)0.0016 (6)0.0036 (6)
C20.0179 (8)0.0219 (8)0.0180 (8)0.0024 (6)0.0018 (6)0.0034 (6)
C30.0190 (8)0.0303 (10)0.0200 (8)0.0011 (7)0.0058 (7)0.0046 (7)
C40.0190 (8)0.0305 (10)0.0224 (8)0.0060 (7)0.0029 (7)0.0082 (7)
C50.0171 (8)0.0241 (9)0.0186 (8)0.0030 (6)0.0012 (6)0.0056 (7)
C60.0244 (9)0.0220 (9)0.0259 (9)0.0077 (7)0.0024 (7)0.0061 (7)
C70.0255 (9)0.0180 (8)0.0261 (9)0.0041 (7)0.0045 (7)0.0021 (7)
C80.0208 (8)0.0198 (8)0.0196 (8)0.0008 (6)0.0029 (7)0.0023 (6)
C90.0262 (9)0.0199 (9)0.0249 (9)0.0019 (7)0.0008 (7)0.0026 (7)
C100.0231 (9)0.0284 (10)0.0213 (8)0.0030 (7)0.0049 (7)0.0022 (7)
C110.0195 (8)0.0244 (9)0.0196 (8)0.0007 (7)0.0045 (7)0.0036 (7)
C120.0170 (7)0.0194 (8)0.0144 (7)0.0011 (6)0.0011 (6)0.0034 (6)
C130.0177 (8)0.0152 (8)0.0170 (7)0.0003 (6)0.0029 (6)0.0012 (6)
C140.0163 (8)0.0208 (8)0.0237 (8)0.0001 (6)0.0009 (7)0.0029 (7)
C150.0151 (8)0.0233 (9)0.0297 (9)0.0017 (6)0.0047 (7)0.0017 (7)
C160.0205 (8)0.0206 (8)0.0273 (9)0.0045 (7)0.0082 (7)0.0030 (7)
C170.0196 (8)0.0172 (8)0.0213 (8)0.0030 (6)0.0050 (7)0.0012 (6)
C180.0271 (9)0.0244 (9)0.0221 (8)0.0049 (7)0.0056 (7)0.0072 (7)
C190.0272 (9)0.0264 (9)0.0185 (8)0.0032 (7)0.0004 (7)0.0073 (7)
C200.0211 (8)0.0191 (8)0.0172 (8)0.0014 (6)0.0016 (6)0.0016 (6)
C210.0215 (8)0.0267 (9)0.0160 (8)0.0002 (7)0.0016 (6)0.0026 (7)
C220.0152 (8)0.0271 (9)0.0197 (8)0.0024 (7)0.0008 (6)0.0006 (7)
C230.0172 (8)0.0218 (8)0.0180 (8)0.0024 (6)0.0031 (6)0.0024 (6)
C240.0180 (8)0.0153 (8)0.0160 (7)0.0015 (6)0.0037 (6)0.0007 (6)
C250.0159 (7)0.0245 (9)0.0173 (8)0.0045 (6)0.0026 (6)0.0050 (7)
C260.0183 (8)0.0264 (9)0.0224 (8)0.0028 (7)0.0043 (7)0.0063 (7)
C270.0180 (8)0.0378 (11)0.0276 (9)0.0058 (7)0.0018 (7)0.0135 (8)
C280.0192 (8)0.0454 (12)0.0228 (9)0.0034 (8)0.0033 (7)0.0107 (8)
C290.0188 (8)0.0350 (10)0.0192 (8)0.0070 (7)0.0004 (7)0.0060 (7)
C300.0306 (10)0.0422 (12)0.0204 (9)0.0141 (9)0.0049 (8)0.0035 (8)
C310.0379 (11)0.0312 (10)0.0228 (9)0.0146 (9)0.0021 (8)0.0029 (8)
C320.0265 (9)0.0237 (9)0.0222 (8)0.0069 (7)0.0048 (7)0.0001 (7)
C330.0352 (10)0.0197 (9)0.0302 (10)0.0037 (8)0.0083 (8)0.0036 (7)
C340.0269 (9)0.0198 (9)0.0347 (10)0.0037 (7)0.0065 (8)0.0031 (8)
C350.0185 (8)0.0200 (8)0.0249 (9)0.0002 (6)0.0024 (7)0.0043 (7)
C360.0172 (8)0.0224 (8)0.0185 (8)0.0053 (6)0.0030 (6)0.0029 (7)
C370.0242 (9)0.0344 (11)0.0268 (9)0.0009 (8)0.0101 (7)0.0069 (8)
C380.0216 (8)0.0236 (9)0.0206 (8)0.0001 (7)0.0021 (7)0.0022 (7)
C390.0282 (10)0.0352 (11)0.0247 (9)0.0015 (8)0.0054 (8)0.0000 (8)
C400.0187 (8)0.0184 (8)0.0195 (8)0.0013 (6)0.0027 (6)0.0036 (6)
C410.0193 (8)0.0189 (8)0.0214 (8)0.0003 (6)0.0022 (6)0.0063 (7)
C420.0157 (8)0.0239 (9)0.0232 (8)0.0000 (6)0.0028 (6)0.0047 (7)
C430.0217 (8)0.0168 (8)0.0276 (9)0.0016 (6)0.0025 (7)0.0052 (7)
C440.0249 (9)0.0220 (9)0.0424 (11)0.0049 (7)0.0017 (8)0.0091 (8)
C450.0383 (11)0.0217 (10)0.0490 (13)0.0068 (8)0.0068 (10)0.0057 (9)
C460.0344 (11)0.0379 (12)0.0513 (14)0.0028 (10)0.0203 (10)0.0030 (10)
C470.0240 (9)0.0381 (11)0.0358 (11)0.0039 (8)0.0032 (8)0.0105 (9)
C480.0282 (10)0.0373 (12)0.0369 (11)0.0086 (8)0.0015 (9)0.0047 (9)
C490.0302 (10)0.0439 (13)0.0373 (11)0.0095 (9)0.0002 (9)0.0121 (10)
C500.0315 (11)0.0494 (13)0.0303 (10)0.0051 (9)0.0002 (8)0.0106 (9)
C510.0304 (11)0.0708 (17)0.0234 (10)0.0104 (11)0.0012 (8)0.0161 (10)
C520.0442 (13)0.0603 (16)0.0316 (12)0.0092 (11)0.0031 (10)0.0149 (11)
O3A0.0271 (9)0.0318 (9)0.0363 (9)0.0006 (7)0.0053 (7)0.0164 (7)
O4A0.125 (3)0.0537 (15)0.101 (2)0.0385 (17)0.075 (2)0.0142 (15)
C53A0.0445 (15)0.0368 (14)0.0493 (16)0.0094 (12)0.0042 (12)0.0190 (12)
C54A0.0388 (13)0.0248 (12)0.0445 (14)0.0119 (10)0.0065 (11)0.0118 (10)
O3B0.029 (4)0.040 (4)0.044 (4)0.020 (4)0.007 (4)0.006 (4)
O4B0.029 (5)0.024 (5)0.027 (5)0.005 (4)0.009 (4)0.002 (4)
C53B0.034 (4)0.028 (4)0.048 (5)0.001 (4)0.011 (4)0.016 (4)
C54B0.037 (4)0.030 (4)0.065 (5)0.007 (4)0.001 (4)0.011 (4)
Geometric parameters (Å, º) top
Fe1—N21.9647 (14)C19—H190.9500
Fe1—N11.9692 (14)C20—C241.397 (2)
Fe1—N51.9724 (14)C20—C211.405 (2)
Fe1—N31.9739 (14)C21—C221.374 (2)
Fe1—N41.9748 (14)C21—H210.9500
Fe1—N61.9769 (14)C22—C231.398 (2)
O1—C401.342 (2)C22—H220.9500
O1—C441.442 (2)C23—H230.9500
O2—C451.401 (3)C25—C291.404 (2)
O2—H1O0.8499C25—C361.423 (2)
O1W—H1W0.8499C26—C271.401 (3)
O1W—H2W0.8500C26—H260.9500
N1—C21.333 (2)C27—C281.365 (3)
N1—C11.365 (2)C27—H270.9500
N2—C111.331 (2)C28—C291.405 (3)
N2—C121.366 (2)C28—H280.9500
N3—C141.328 (2)C29—C301.432 (3)
N3—C131.363 (2)C30—C311.349 (3)
N4—C231.327 (2)C30—H300.9500
N4—C241.368 (2)C31—C321.435 (3)
N5—C261.335 (2)C31—H310.9500
N5—C251.364 (2)C32—C361.400 (2)
N6—C351.332 (2)C32—C331.405 (3)
N6—C361.368 (2)C33—C341.367 (3)
N7—C371.146 (3)C33—H330.9500
N8—C391.148 (3)C34—C351.403 (3)
N9—C431.150 (2)C34—H340.9500
N10—C421.148 (2)C35—H350.9500
N11—C461.156 (3)C37—C381.418 (3)
N12—C481.146 (3)C38—C401.398 (2)
N13—C521.150 (3)C38—C391.421 (3)
N14—C511.141 (3)C40—C411.401 (2)
C1—C51.401 (2)C41—C421.418 (2)
C1—C121.423 (2)C41—C431.421 (2)
C2—C31.402 (2)C44—C451.501 (3)
C2—H20.9500C44—H44A0.9900
C3—C41.369 (3)C44—H44B0.9900
C3—H30.9500C45—H45A0.9900
C4—C51.409 (2)C45—H45B0.9900
C4—H40.9500C46—C471.413 (3)
C5—C61.434 (2)C47—C491.383 (3)
C6—C71.352 (3)C47—C481.427 (3)
C6—H60.9500C49—O3A1.373 (3)
C7—C81.437 (2)C49—C501.393 (3)
C7—H70.9500C49—O3B1.413 (5)
C8—C121.398 (2)C50—C511.415 (3)
C8—C91.406 (2)C50—C521.420 (3)
C9—C101.373 (3)O3A—C53A1.424 (3)
C9—H90.9500O4A—C54A1.401 (3)
C10—C111.398 (3)O4A—H2OA0.8500
C10—H100.9500C53A—C54A1.507 (4)
C11—H110.9500C53A—H53A0.9900
C13—C171.405 (2)C53A—H53B0.9900
C13—C241.421 (2)C54A—H54A0.9900
C14—C151.400 (2)C54A—H54B0.9900
C14—H140.9500O3B—C53B1.430 (6)
C15—C161.366 (3)O4B—C54B1.412 (6)
C15—H150.9500O4B—H2OB0.8500
C16—C171.404 (2)C53B—C54B1.512 (6)
C16—H160.9500C53B—H53C0.9900
C17—C181.432 (2)C53B—H53D0.9900
C18—C191.355 (3)C54B—H54C0.9900
C18—H180.9500C54B—H54D0.9900
C19—C201.434 (2)
N2—Fe1—N182.92 (6)N4—C24—C13115.66 (14)
N2—Fe1—N593.10 (6)C20—C24—C13120.43 (14)
N1—Fe1—N590.51 (5)N5—C25—C29123.69 (16)
N2—Fe1—N393.84 (6)N5—C25—C36115.98 (15)
N1—Fe1—N3175.64 (6)C29—C25—C36120.33 (16)
N5—Fe1—N392.58 (6)N5—C26—C27122.43 (17)
N2—Fe1—N491.09 (6)N5—C26—H26118.8
N1—Fe1—N494.44 (5)C27—C26—H26118.8
N5—Fe1—N4173.87 (6)C28—C27—C26120.18 (17)
N3—Fe1—N482.68 (6)C28—C27—H27119.9
N2—Fe1—N6174.39 (6)C26—C27—H27119.9
N1—Fe1—N693.21 (6)C27—C28—C29119.24 (17)
N5—Fe1—N682.85 (6)C27—C28—H28120.4
N3—Fe1—N690.22 (6)C29—C28—H28120.4
N4—Fe1—N693.26 (6)C25—C29—C28117.14 (17)
C40—O1—C44122.74 (13)C25—C29—C30118.25 (17)
C45—O2—H1O108.6C28—C29—C30124.61 (17)
H1W—O1W—H2W108.4C31—C30—C29121.38 (17)
C2—N1—C1117.44 (14)C31—C30—H30119.3
C2—N1—Fe1129.87 (12)C29—C30—H30119.3
C1—N1—Fe1112.68 (10)C30—C31—C32121.34 (18)
C11—N2—C12116.91 (15)C30—C31—H31119.3
C11—N2—Fe1130.04 (12)C32—C31—H31119.3
C12—N2—Fe1113.04 (11)C36—C32—C33117.18 (17)
C14—N3—C13117.17 (14)C36—C32—C31118.22 (17)
C14—N3—Fe1130.00 (12)C33—C32—C31124.60 (18)
C13—N3—Fe1112.81 (11)C34—C33—C32119.11 (17)
C23—N4—C24116.92 (14)C34—C33—H33120.4
C23—N4—Fe1130.38 (11)C32—C33—H33120.4
C24—N4—Fe1112.70 (11)C33—C34—C35120.19 (17)
C26—N5—C25117.31 (15)C33—C34—H34119.9
C26—N5—Fe1129.92 (13)C35—C34—H34119.9
C25—N5—Fe1112.75 (11)N6—C35—C34122.46 (17)
C35—N6—C36117.18 (15)N6—C35—H35118.8
C35—N6—Fe1130.19 (12)C34—C35—H35118.8
C36—N6—Fe1112.63 (11)N6—C36—C32123.87 (16)
N1—C1—C5123.90 (15)N6—C36—C25115.68 (15)
N1—C1—C12115.83 (14)C32—C36—C25120.44 (16)
C5—C1—C12120.27 (15)N7—C37—C38176.7 (2)
N1—C2—C3122.34 (16)C40—C38—C37124.17 (16)
N1—C2—H2118.8C40—C38—C39118.48 (16)
C3—C2—H2118.8C37—C38—C39116.90 (16)
C4—C3—C2120.18 (16)N8—C39—C38178.7 (2)
C4—C3—H3119.9O1—C40—C38112.04 (15)
C2—C3—H3119.9O1—C40—C41121.79 (15)
C3—C4—C5119.16 (16)C38—C40—C41126.09 (16)
C3—C4—H4120.4C40—C41—C42122.11 (15)
C5—C4—H4120.4C40—C41—C43123.75 (15)
C1—C5—C4116.97 (16)C42—C41—C43114.01 (15)
C1—C5—C6118.36 (15)N10—C42—C41176.29 (18)
C4—C5—C6124.67 (16)N9—C43—C41176.56 (19)
C7—C6—C5121.37 (16)O1—C44—C45105.29 (15)
C7—C6—H6119.3O1—C44—H44A110.7
C5—C6—H6119.3C45—C44—H44A110.7
C6—C7—C8121.09 (16)O1—C44—H44B110.7
C6—C7—H7119.5C45—C44—H44B110.7
C8—C7—H7119.5H44A—C44—H44B108.8
C12—C8—C9117.21 (16)O2—C45—C44112.30 (18)
C12—C8—C7118.32 (16)O2—C45—H45A109.1
C9—C8—C7124.47 (16)C44—C45—H45A109.1
C10—C9—C8119.05 (16)O2—C45—H45B109.1
C10—C9—H9120.5C44—C45—H45B109.1
C8—C9—H9120.5H45A—C45—H45B107.9
C9—C10—C11119.78 (16)N11—C46—C47177.2 (3)
C9—C10—H10120.1C49—C47—C46123.68 (19)
C11—C10—H10120.1C49—C47—C48119.72 (19)
N2—C11—C10123.06 (16)C46—C47—C48116.6 (2)
N2—C11—H11118.5N12—C48—C47178.8 (3)
C10—C11—H11118.5O3A—C49—C47115.26 (19)
N2—C12—C8123.98 (15)O3A—C49—C50115.3 (2)
N2—C12—C1115.43 (15)C47—C49—C50129.2 (2)
C8—C12—C1120.59 (15)C47—C49—O3B114.5 (5)
N3—C13—C17123.88 (15)C50—C49—O3B107.7 (5)
N3—C13—C24115.90 (14)C49—C50—C51123.5 (2)
C17—C13—C24120.20 (15)C49—C50—C52119.3 (2)
N3—C14—C15122.55 (16)C51—C50—C52117.1 (2)
N3—C14—H14118.7N14—C51—C50177.5 (2)
C15—C14—H14118.7N13—C52—C50179.9 (3)
C16—C15—C14120.44 (16)C49—O3A—C53A113.68 (18)
C16—C15—H15119.8C54A—O4A—H2OA109.2
C14—C15—H15119.8O3A—C53A—C54A105.6 (2)
C15—C16—C17118.83 (15)O3A—C53A—H53A110.6
C15—C16—H16120.6C54A—C53A—H53A110.6
C17—C16—H16120.6O3A—C53A—H53B110.6
C16—C17—C13117.12 (16)C54A—C53A—H53B110.6
C16—C17—C18124.29 (15)H53A—C53A—H53B108.7
C13—C17—C18118.58 (15)O4A—C54A—C53A111.5 (2)
C19—C18—C17120.94 (16)O4A—C54A—H54A109.3
C19—C18—H18119.5C53A—C54A—H54A109.3
C17—C18—H18119.5O4A—C54A—H54B109.3
C18—C19—C20121.24 (16)C53A—C54A—H54B109.3
C18—C19—H19119.4H54A—C54A—H54B108.0
C20—C19—H19119.4C49—O3B—C53B115.2 (8)
C24—C20—C21117.46 (15)C54B—O4B—H2OB111.4
C24—C20—C19118.53 (15)O3B—C53B—C54B120.9 (11)
C21—C20—C19124.00 (16)O3B—C53B—H53C107.1
C22—C21—C20118.56 (15)C54B—C53B—H53C107.1
C22—C21—H21120.7O3B—C53B—H53D107.1
C20—C21—H21120.7C54B—C53B—H53D107.1
C21—C22—C23120.13 (16)H53C—C53B—H53D106.8
C21—C22—H22119.9O4B—C54B—C53B106.2 (10)
C23—C22—H22119.9O4B—C54B—H54C110.5
N4—C23—C22122.91 (15)C53B—C54B—H54C110.5
N4—C23—H23118.5O4B—C54B—H54D110.5
C22—C23—H23118.5C53B—C54B—H54D110.5
N4—C24—C20123.90 (15)H54C—C54B—H54D108.7
N2—Fe1—N1—C2178.69 (15)N3—C13—C17—C18179.45 (16)
N5—Fe1—N1—C288.25 (15)C24—C13—C17—C182.5 (2)
N4—Fe1—N1—C288.13 (14)C16—C17—C18—C19178.68 (18)
N6—Fe1—N1—C25.39 (15)C13—C17—C18—C191.0 (3)
N2—Fe1—N1—C12.84 (11)C17—C18—C19—C201.7 (3)
N5—Fe1—N1—C190.22 (11)C18—C19—C20—C242.9 (3)
N4—Fe1—N1—C193.40 (11)C18—C19—C20—C21175.77 (18)
N6—Fe1—N1—C1173.08 (11)C24—C20—C21—C221.7 (2)
N1—Fe1—N2—C11178.41 (15)C19—C20—C21—C22176.98 (17)
N5—Fe1—N2—C1191.46 (15)C20—C21—C22—C233.1 (3)
N3—Fe1—N2—C111.33 (15)C24—N4—C23—C221.5 (2)
N4—Fe1—N2—C1184.07 (15)Fe1—N4—C23—C22178.67 (12)
N1—Fe1—N2—C122.24 (11)C21—C22—C23—N41.6 (3)
N5—Fe1—N2—C1287.89 (11)C23—N4—C24—C203.0 (2)
N3—Fe1—N2—C12179.32 (11)Fe1—N4—C24—C20177.09 (13)
N4—Fe1—N2—C1296.58 (11)C23—N4—C24—C13175.88 (15)
N2—Fe1—N3—C1486.56 (15)Fe1—N4—C24—C134.02 (18)
N5—Fe1—N3—C146.72 (16)C21—C20—C24—N41.5 (2)
N4—Fe1—N3—C14177.17 (16)C19—C20—C24—N4179.82 (15)
N6—Fe1—N3—C1489.57 (15)C21—C20—C24—C13177.38 (15)
N2—Fe1—N3—C1394.75 (11)C19—C20—C24—C131.3 (2)
N5—Fe1—N3—C13171.97 (11)N3—C13—C24—N40.6 (2)
N4—Fe1—N3—C134.13 (11)C17—C13—C24—N4177.63 (15)
N6—Fe1—N3—C1389.12 (12)N3—C13—C24—C20179.53 (15)
N2—Fe1—N4—C2381.70 (15)C17—C13—C24—C201.3 (2)
N1—Fe1—N4—C231.28 (15)C26—N5—C25—C291.2 (2)
N3—Fe1—N4—C23175.44 (16)Fe1—N5—C25—C29177.37 (13)
N6—Fe1—N4—C2394.76 (15)C26—N5—C25—C36178.73 (14)
N2—Fe1—N4—C2498.18 (11)Fe1—N5—C25—C362.74 (17)
N1—Fe1—N4—C24178.84 (11)C25—N5—C26—C270.5 (2)
N3—Fe1—N4—C244.45 (11)Fe1—N5—C26—C27177.76 (13)
N6—Fe1—N4—C2485.36 (11)N5—C26—C27—C280.5 (3)
N2—Fe1—N5—C262.50 (15)C26—C27—C28—C290.7 (3)
N1—Fe1—N5—C2685.43 (15)N5—C25—C29—C280.9 (2)
N3—Fe1—N5—C2691.49 (15)C36—C25—C29—C28178.99 (15)
N6—Fe1—N5—C26178.61 (15)N5—C25—C29—C30179.70 (15)
N2—Fe1—N5—C25179.21 (11)C36—C25—C29—C300.4 (2)
N1—Fe1—N5—C2596.28 (11)C27—C28—C29—C250.1 (3)
N3—Fe1—N5—C2586.80 (11)C27—C28—C29—C30179.28 (17)
N6—Fe1—N5—C253.10 (11)C25—C29—C30—C311.2 (3)
N1—Fe1—N6—C3587.10 (15)C28—C29—C30—C31178.13 (18)
N5—Fe1—N6—C35177.22 (15)C29—C30—C31—C320.5 (3)
N3—Fe1—N6—C3590.22 (15)C30—C31—C32—C361.1 (3)
N4—Fe1—N6—C357.53 (15)C30—C31—C32—C33178.55 (18)
N1—Fe1—N6—C3693.05 (11)C36—C32—C33—C340.3 (3)
N5—Fe1—N6—C362.94 (11)C31—C32—C33—C34179.89 (18)
N3—Fe1—N6—C3689.63 (11)C32—C33—C34—C350.6 (3)
N4—Fe1—N6—C36172.31 (11)C36—N6—C35—C340.3 (2)
C2—N1—C1—C50.7 (2)Fe1—N6—C35—C34179.58 (13)
Fe1—N1—C1—C5177.95 (13)C33—C34—C35—N60.6 (3)
C2—N1—C1—C12178.36 (14)C35—N6—C36—C321.2 (2)
Fe1—N1—C1—C122.97 (17)Fe1—N6—C36—C32178.69 (13)
C1—N1—C2—C30.3 (2)C35—N6—C36—C25177.84 (14)
Fe1—N1—C2—C3178.13 (12)Fe1—N6—C36—C252.29 (17)
N1—C2—C3—C40.2 (3)C33—C32—C36—N61.2 (3)
C2—C3—C4—C50.3 (3)C31—C32—C36—N6179.17 (15)
N1—C1—C5—C40.6 (2)C33—C32—C36—C25177.78 (15)
C12—C1—C5—C4178.42 (15)C31—C32—C36—C251.9 (2)
N1—C1—C5—C6179.85 (15)N5—C25—C36—N60.3 (2)
C12—C1—C5—C60.8 (2)C29—C25—C36—N6179.81 (14)
C3—C4—C5—C10.1 (2)N5—C25—C36—C32178.76 (15)
C3—C4—C5—C6179.25 (17)C29—C25—C36—C321.1 (2)
C1—C5—C6—C71.0 (3)C44—O1—C40—C38147.72 (17)
C4—C5—C6—C7178.11 (17)C44—O1—C40—C4135.1 (2)
C5—C6—C7—C80.5 (3)C37—C38—C40—O1162.11 (17)
C6—C7—C8—C120.3 (3)C39—C38—C40—O19.9 (2)
C6—C7—C8—C9179.17 (17)C37—C38—C40—C4114.9 (3)
C12—C8—C9—C100.7 (2)C39—C38—C40—C41173.01 (17)
C7—C8—C9—C10179.82 (17)O1—C40—C41—C42168.39 (16)
C8—C9—C10—C110.2 (3)C38—C40—C41—C4214.8 (3)
C12—N2—C11—C100.0 (2)O1—C40—C41—C4316.1 (3)
Fe1—N2—C11—C10179.29 (13)C38—C40—C41—C43160.71 (18)
C9—C10—C11—N20.5 (3)C40—O1—C44—C45155.79 (16)
C11—N2—C12—C81.0 (2)O1—C44—C45—O263.3 (2)
Fe1—N2—C12—C8178.44 (13)C46—C47—C49—O3A172.8 (2)
C11—N2—C12—C1179.29 (14)C48—C47—C49—O3A5.0 (3)
Fe1—N2—C12—C11.27 (17)C46—C47—C49—C501.0 (4)
C9—C8—C12—N21.3 (2)C48—C47—C49—C50178.8 (2)
C7—C8—C12—N2179.14 (15)C46—C47—C49—O3B144.3 (5)
C9—C8—C12—C1178.98 (15)C48—C47—C49—O3B37.8 (5)
C7—C8—C12—C10.6 (2)O3A—C49—C50—C51167.3 (2)
N1—C1—C12—N21.1 (2)C47—C49—C50—C516.4 (4)
C5—C1—C12—N2179.74 (14)O3B—C49—C50—C51151.7 (5)
N1—C1—C12—C8179.14 (14)O3A—C49—C50—C529.9 (3)
C5—C1—C12—C80.0 (2)C47—C49—C50—C52176.3 (2)
C14—N3—C13—C170.2 (2)O3B—C49—C50—C5231.1 (5)
Fe1—N3—C13—C17178.71 (13)C47—C49—O3A—C53A85.4 (3)
C14—N3—C13—C24177.99 (15)C50—C49—O3A—C53A99.9 (3)
Fe1—N3—C13—C243.13 (18)O3B—C49—O3A—C53A12.9 (7)
C13—N3—C14—C150.4 (2)C49—O3A—C53A—C54A161.2 (2)
Fe1—N3—C14—C15179.04 (13)O3A—C53A—C54A—O4A61.2 (3)
N3—C14—C15—C160.2 (3)O3A—C49—O3B—C53B1.4 (8)
C14—C15—C16—C170.5 (3)C47—C49—O3B—C53B101.9 (11)
C15—C16—C17—C131.0 (2)C50—C49—O3B—C53B107.1 (10)
C15—C16—C17—C18179.33 (17)C49—O3B—C53B—C54B155.5 (11)
N3—C13—C17—C160.9 (2)O3B—C53B—C54B—O4B64.2 (19)
C24—C13—C17—C16177.22 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O···O1W0.852.012.833 (2)164
O1W—H1W···N80.852.383.190 (3)160
O1W—H2W···N120.852.142.952 (2)159
O4A—H2OA···N13i0.852.443.289 (5)175
O4B—H2OB···N9ii0.852.243.023 (9)154
C10—H10···N8iii0.952.453.376 (3)166
C15—H15···N110.952.573.189 (3)123
C19—H19···N10iv0.952.563.403 (3)148
C21—H21···N10iv0.952.613.439 (2)146
C28—H28···N14v0.952.483.224 (3)135
C35—H35···O20.952.383.132 (2)136
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x+1, y+1, z; (iv) x+2, y, z; (v) x, y+1, z+1.
ππ contacts (Å, °) for (I) top
Rings A, B and C are labelled according to Fig. 2. IPD is the interplanar distance (distance from one plane to the neighbouring centroid), CCD is centre-to-centre distance (distance between ring centroids) and SA is the slippage angle (angle subtended by the intercentroid vector to the plane normal); for details, see Janiak (2000).
Group 1/group 2IPD (Å)CCD (Å)SA (°)
Ring A/ring Aiii(single stack)3.550 (2)3.792 (3)20.58 (5)
Ring B/ring Cvi(double stack)3.498 (2)3.939 (3)27.37 (5)
Symmetry codes: (iii) -x + 1, -y + 1, -z; (vi) -x + 1, -y + 1, -z + 1.
Selected bond lengths (Å) and Wiberg bond orders for tcnoetOH- anions from X-ray data and DFT calculations top
The calculations were performed at the B97D/6-311+G(2d,2p) level of theory. For details of Wiberg bond-order calculations, see Wiberg (1968).
ParameterBond lengthWiberg bond order
N7—C371.146 (3)2.783
N8—C391.148 (3)2.767
N9—C431.150 (2)2.767
N10—C421.148 (2)2.781
N11—C461.156 (3)2.785
N12—C481.146 (3)2.758
N13—C521.150 (3)2.784
N14—C511.141 (3)2.788
C37—C381.418 (3)1.130
C38—C401.398 (2)1.298
C38—C391.421 (3)1.132
C40—C411.401 (2)1.285
C41—C421.418 (2)1.126
C41—C431.421 (2)1.138
C46—C471.413 (3)1.127
C47—C491.383 (3)1.320
C47—C481.427 (3)1.128
C49—C501.393 (3)1.326
C50—C511.415 (3)1.125
C50—C521.420 (3)1.125
 

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